EP0306398A1 - Chemisches Verfahren zur Vernichtung von halogenierten organischen Produkten - Google Patents
Chemisches Verfahren zur Vernichtung von halogenierten organischen Produkten Download PDFInfo
- Publication number
- EP0306398A1 EP0306398A1 EP19880402176 EP88402176A EP0306398A1 EP 0306398 A1 EP0306398 A1 EP 0306398A1 EP 19880402176 EP19880402176 EP 19880402176 EP 88402176 A EP88402176 A EP 88402176A EP 0306398 A1 EP0306398 A1 EP 0306398A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- products
- alcoholate
- ppm
- halogenated organic
- organic products
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000006378 damage Effects 0.000 title abstract description 5
- 238000001311 chemical methods and process Methods 0.000 title description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 150000003071 polychlorinated biphenyls Chemical class 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000002013 dioxins Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000004826 dibenzofurans Chemical class 0.000 claims description 2
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical class C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 150000004961 triphenylmethanes Chemical class 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 6
- 239000012530 fluid Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 42
- 235000017168 chlorine Nutrition 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- -1 polyarylalkanes Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MEIUXJOXEUYBRW-UHFFFAOYSA-N 1,2-dichloro-3-(1,1-dichloro-2-phenylethyl)benzene Chemical compound ClC1=CC=CC(C(Cl)(Cl)CC=2C=CC=CC=2)=C1Cl MEIUXJOXEUYBRW-UHFFFAOYSA-N 0.000 description 2
- WZTJFRVXSHGGEF-UHFFFAOYSA-N 1-chloro-4-(2-phenylethyl)benzene Chemical compound C1=CC(Cl)=CC=C1CCC1=CC=CC=C1 WZTJFRVXSHGGEF-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010408 sweeping Methods 0.000 description 2
- NDRKXFLZSRHAJE-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4-tribromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=CC=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br NDRKXFLZSRHAJE-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910001504 inorganic chloride Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/34—Dehalogenation using reactive chemical agents able to degrade
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
- B09B—DISPOSAL OF SOLID WASTE NOT OTHERWISE PROVIDED FOR
- B09B3/00—Destroying solid waste or transforming solid waste into something useful or harmless
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/22—Organic substances containing halogen
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
Definitions
- the present invention relates to a chemical process for destroying halogenated organic products and more particularly chlorinated aromatic products such as for example PCBs (polychlorinated biphenyls) optionally mixed with non-chlorinated organic products.
- chlorinated aromatic products such as for example PCBs (polychlorinated biphenyls) optionally mixed with non-chlorinated organic products.
- European patent application EP 21294 describes the destruction of dioxins, in particular chlorinated anisoles containing 39.7 ppm of 2,3,7,8-tetrachlorodibenzo-p-dioxin, by reacting these products under pressure with sodium methylate in methanol at 160 ° C.
- dioxins in particular chlorinated anisoles containing 39.7 ppm of 2,3,7,8-tetrachlorodibenzo-p-dioxin
- the invention relates to all halogenated products but more particularly to products containing aryl carbons substituted with chlorine and / or bromine.
- this family we find for example chlorinated or brominated dioxins, chlorinated dibenzofurans or brominated, the (polychloro) biphenyls, the (polybromo) biphenyls, the (polybromo) diphenyl ethers, the (polychloro) diphenyl ethers.
- These products can be pure or mixed together or as a mixture with non-halogenated organic products, such as polyarylalkanes, mineral oils.
- the invention allows the destruction of any halogenated product, it is advantageously used for products containing less than 1% by weight of halogen and preferably less than 1000 ppm.
- any alcoholate derived from a monoalcohol, a diol or a triol and an alkali metal can be used and among them the methylates and glycol alcoholate or polyglycol, methylate, ethylate are advantageously used , sodium, lithium or potassium propylate or isopropylate or a mixture of these products and preferably sodium methylate.
- the alcoholate is added to the halogenated products or to the mixture containing the halogenated products.
- powdered sodium methylate is used.
- the stoichiometry being an alcoholate function per halogen atom to be eliminated, an amount of alcoholate is used in excess with respect to this stoichiometry. Very good dehalogenation is obtained by using an excess of 5 to 10 times the stoichiometry. For example, if a mixture contains PCBs in proportion to 100 ppm expressed as chlorine, an amount of sodium methylate of 0.14% is used.
- the halogenated organic products are brought into contact with the alcoholate with stirring, for example in a stirred reactor or a packed column, or any other device allowing sufficient stirring so that the alcoholate is well dispersed and is in contact with the products. halogenated the time necessary for their destruction.
- the reaction can be carried out continuously or batchwise.
- the reaction kinetics increase with temperature. It is possible to use a temperature between 220 and 300 ° C., it is preferred to operate between 250 and 290 ° C. Depending on the physical properties of the products (ten steam) is operated at atmospheric pressure or at higher pressure.
- the reaction time is a function of the amounts of organic halogen, the temperature, the amount of alcoholate, the stirring conditions to effect good contacting of the reagents; it is usually between 30 minutes and 10 hours.
- the invention is particularly useful for destroying aryl halogenated products contained in a mixture, for example a non-halogen dielectric liquid or a mineral oil containing PCBs.
- a mixture for example a non-halogen dielectric liquid or a mineral oil containing PCBs.
- the process of the invention is applied to this product containing PCBs or other chlorinated products, then the inorganic halogenated products are separated for example by distillation from the other products.
- a mineral oil is thus obtained, a dielectric free from organic chlorine.
- the process of the present invention is also used in addition to a sodium carbonate process.
- Sodium carbonate is very easy to handle but only removes aliphatic halogens as well as the most labile aryl halogens.
- the process of the invention makes it possible to obtain a product with an aryl halogen content of less than 10 ppm.
- the advantage of this process is that, although it applies to products having poorly reactive halogen atoms, it does not require the use of solvents; That is to say, it suffices to add an alcoholate for example to the oil containing the PCBs without having to add, in addition to the alcoholate, alcohol corresponding to the alcoholate as in EP 21294.
- This process does not require at the end of treatment, before recovering the products free of aryl halogens, of prior separation of the excess alcoholate, in particular sodium methylate.
- Another advantage of the process is that the by-products formed such as NaCl chloride, halogenated aryl products transformed by the alcoholate and the remainder of unreacted alcoholate can be easily destroyed by incineration without generating toxic products.
- DBT dibenzyltoluene
- This mixture is placed in a reactor fitted with rotary agitation, an ascending cooler and a nitrogen injector. After sweeping for 15 minutes with a stream of nitrogen at 100 ° C., 1% by weight (ie 10 g) of sodium methylate is added. The medium is brought to reflux at 285 ° C., with stirring and flushing with nitrogen for 3 hours. The product is then distilled with progressive vacuuming up to 2 mm of mercury so as not to exceed 300 ° C in the bottom. The distillate obtained has a total aromatic chlorine content of 3 ppm.
- Example 2 DBT is treated as in Example 1 but with NaOC2H5, KOCH3, KOC2H5, NaOCH (CH3) 2, under the conditions of Example 1. The results are shown in the table.
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fire-Extinguishing Compositions (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Insulating Materials (AREA)
- Processing Of Solid Wastes (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT88402176T ATE85229T1 (de) | 1987-09-03 | 1988-08-29 | Chemisches verfahren zur vernichtung von halogenierten organischen produkten. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8712248 | 1987-09-03 | ||
| FR8712248A FR2620055B1 (fr) | 1987-09-03 | 1987-09-03 | Procede chimique de destruction de produits organiques halogenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0306398A1 true EP0306398A1 (de) | 1989-03-08 |
| EP0306398B1 EP0306398B1 (de) | 1993-02-03 |
Family
ID=9354601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88402176A Expired - Lifetime EP0306398B1 (de) | 1987-09-03 | 1988-08-29 | Chemisches Verfahren zur Vernichtung von halogenierten organischen Produkten |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0306398B1 (de) |
| JP (1) | JPH0667409B2 (de) |
| KR (1) | KR910000196B1 (de) |
| CN (1) | CN1016142B (de) |
| AT (1) | ATE85229T1 (de) |
| CA (1) | CA1336981C (de) |
| DE (1) | DE3878098T2 (de) |
| DK (1) | DK169377B1 (de) |
| ES (1) | ES2053784T3 (de) |
| FI (1) | FI97276C (de) |
| FR (1) | FR2620055B1 (de) |
| IE (1) | IE63083B1 (de) |
| NO (1) | NO176749C (de) |
| PT (1) | PT88421B (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0435737A1 (de) | 1989-12-28 | 1991-07-03 | Elf Atochem S.A. | Verfahren zur Synthese von Benzyltoluol und Dibenzyltoluol mit niedrigem Chlorgehalt |
| EP0491452A1 (de) * | 1990-12-12 | 1992-06-24 | Chemical Waste Management, Inc. | Verfahren zur Dehalogenierung |
| EP0506153A1 (de) * | 1991-03-23 | 1992-09-30 | METALLGESELLSCHAFT Aktiengesellschaft | Verfahren zur Zersetzung von polyhalogenierten Organoverbindungen |
| US5490919A (en) * | 1990-08-14 | 1996-02-13 | State Of Isreal, Atomic Energy Commission | Process for the dehalogenation of organic compounds |
| EP1630824A1 (de) | 1994-09-30 | 2006-03-01 | Arkema | Dielektrische Zusammensetzung auf Basis von Polyarylalkanen mit verbesserten dielektrischen Eigenschaften |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04253875A (ja) * | 1991-02-01 | 1992-09-09 | Chiyoda Kohan Kk | クロロホルム又はクロロジフルオロメタンの分解除去方法 |
| JP2638483B2 (ja) * | 1994-06-30 | 1997-08-06 | 株式会社関西テック | 多塩素化芳香族化合物の処理方法 |
| JP4537539B2 (ja) * | 2000-06-20 | 2010-09-01 | 利夫 半谷 | 有害物質の分解処理方法と処理設備 |
| JP2003001220A (ja) * | 2001-06-25 | 2003-01-07 | Kansai Electric Power Co Inc:The | 汚染物からの多塩素化芳香族化合物分離方法 |
| PL2753202T3 (pl) | 2011-09-06 | 2016-11-30 | Podgrzewanie materiału przeznaczonego do palenia | |
| GB201217067D0 (en) | 2012-09-25 | 2012-11-07 | British American Tobacco Co | Heating smokable material |
| GB201311620D0 (en) | 2013-06-28 | 2013-08-14 | British American Tobacco Co | Devices Comprising a Heat Source Material and Activation Chambers for the Same |
| GB201500582D0 (en) | 2015-01-14 | 2015-02-25 | British American Tobacco Co | Apparatus for heating or cooling a material contained therein |
| US20170055584A1 (en) | 2015-08-31 | 2017-03-02 | British American Tobacco (Investments) Limited | Article for use with apparatus for heating smokable material |
| US11924930B2 (en) | 2015-08-31 | 2024-03-05 | Nicoventures Trading Limited | Article for use with apparatus for heating smokable material |
| US20170055575A1 (en) | 2015-08-31 | 2017-03-02 | British American Tobacco (Investments) Limited | Material for use with apparatus for heating smokable material |
| US20170119046A1 (en) | 2015-10-30 | 2017-05-04 | British American Tobacco (Investments) Limited | Apparatus for Heating Smokable Material |
| US20170119047A1 (en) | 2015-10-30 | 2017-05-04 | British American Tobacco (Investments) Limited | Article for Use with Apparatus for Heating Smokable Material |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021294A1 (de) * | 1979-06-15 | 1981-01-07 | Vertac Chemical Corporation | Chemische Entgiftung giftiger chlorierter aromatischer Verbindungen |
| EP0118858A1 (de) * | 1983-03-10 | 1984-09-19 | SEA MARCONI DECONTAMINATION S.r.l. | Verfahren zur Zersetzung und Entgiftung von organischen Stoffen und halogenierten giftigen Materialien |
| US4574013A (en) * | 1985-04-18 | 1986-03-04 | Galson Research Corporation | Method for decontaminating soil |
| EP0225849A1 (de) * | 1985-12-06 | 1987-06-16 | Ciba-Geigy Ag | Verfahren zur Enthalogenierung von halogenierten aliphatischen und aromatischen Verbindungen |
| EP0250748A1 (de) * | 1986-06-25 | 1988-01-07 | Hüls Aktiengesellschaft | Verfahren zur Enthalogenierung von Kohlenwasserstoffölen |
-
1987
- 1987-09-03 FR FR8712248A patent/FR2620055B1/fr not_active Expired - Lifetime
-
1988
- 1988-08-23 CA CA000575896A patent/CA1336981C/fr not_active Expired - Lifetime
- 1988-08-29 EP EP88402176A patent/EP0306398B1/de not_active Expired - Lifetime
- 1988-08-29 AT AT88402176T patent/ATE85229T1/de not_active IP Right Cessation
- 1988-08-29 DE DE8888402176T patent/DE3878098T2/de not_active Expired - Lifetime
- 1988-08-29 ES ES88402176T patent/ES2053784T3/es not_active Expired - Lifetime
- 1988-09-01 JP JP63219600A patent/JPH0667409B2/ja not_active Expired - Lifetime
- 1988-09-01 NO NO883893A patent/NO176749C/no not_active IP Right Cessation
- 1988-09-02 DK DK488488A patent/DK169377B1/da not_active IP Right Cessation
- 1988-09-02 PT PT88421A patent/PT88421B/pt not_active IP Right Cessation
- 1988-09-02 IE IE267088A patent/IE63083B1/en not_active IP Right Cessation
- 1988-09-02 FI FI884055A patent/FI97276C/fi not_active IP Right Cessation
- 1988-09-03 KR KR1019880011407A patent/KR910000196B1/ko not_active IP Right Cessation
- 1988-09-03 CN CN88106409A patent/CN1016142B/zh not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021294A1 (de) * | 1979-06-15 | 1981-01-07 | Vertac Chemical Corporation | Chemische Entgiftung giftiger chlorierter aromatischer Verbindungen |
| EP0118858A1 (de) * | 1983-03-10 | 1984-09-19 | SEA MARCONI DECONTAMINATION S.r.l. | Verfahren zur Zersetzung und Entgiftung von organischen Stoffen und halogenierten giftigen Materialien |
| US4574013A (en) * | 1985-04-18 | 1986-03-04 | Galson Research Corporation | Method for decontaminating soil |
| EP0225849A1 (de) * | 1985-12-06 | 1987-06-16 | Ciba-Geigy Ag | Verfahren zur Enthalogenierung von halogenierten aliphatischen und aromatischen Verbindungen |
| EP0250748A1 (de) * | 1986-06-25 | 1988-01-07 | Hüls Aktiengesellschaft | Verfahren zur Enthalogenierung von Kohlenwasserstoffölen |
Non-Patent Citations (1)
| Title |
|---|
| THE JOURNAL OF ORGANIC CHEMISTRY, vol. 44, no. 26, 21 décembre 1979, pages 4979-4981, American Chemical Society, Easton, PA., US; B.V. LAP et al.: "Sodium-ethanol: A superior reagent for the reductive dehalogenation of polychlorinated alicyclic molecules" * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0435737A1 (de) | 1989-12-28 | 1991-07-03 | Elf Atochem S.A. | Verfahren zur Synthese von Benzyltoluol und Dibenzyltoluol mit niedrigem Chlorgehalt |
| FR2656603A1 (fr) * | 1989-12-28 | 1991-07-05 | Atochem | Procedes de synthese de benzyltoluene et dibenzyltoluene a faible teneur en chlore. |
| US5490919A (en) * | 1990-08-14 | 1996-02-13 | State Of Isreal, Atomic Energy Commission | Process for the dehalogenation of organic compounds |
| EP0491452A1 (de) * | 1990-12-12 | 1992-06-24 | Chemical Waste Management, Inc. | Verfahren zur Dehalogenierung |
| EP0506153A1 (de) * | 1991-03-23 | 1992-09-30 | METALLGESELLSCHAFT Aktiengesellschaft | Verfahren zur Zersetzung von polyhalogenierten Organoverbindungen |
| EP1630824A1 (de) | 1994-09-30 | 2006-03-01 | Arkema | Dielektrische Zusammensetzung auf Basis von Polyarylalkanen mit verbesserten dielektrischen Eigenschaften |
Also Published As
| Publication number | Publication date |
|---|---|
| FI884055A0 (fi) | 1988-09-02 |
| CN1016142B (zh) | 1992-04-08 |
| KR910000196B1 (ko) | 1991-01-23 |
| DK488488D0 (da) | 1988-09-02 |
| DK488488A (da) | 1989-03-04 |
| CA1336981C (fr) | 1995-09-12 |
| CN1032109A (zh) | 1989-04-05 |
| DE3878098D1 (de) | 1993-03-18 |
| FR2620055A1 (fr) | 1989-03-10 |
| DK169377B1 (da) | 1994-10-17 |
| NO883893D0 (no) | 1988-09-01 |
| ES2053784T3 (es) | 1994-08-01 |
| FR2620055B1 (fr) | 1991-05-10 |
| FI97276B (fi) | 1996-08-15 |
| IE63083B1 (en) | 1995-03-22 |
| PT88421A (pt) | 1989-07-31 |
| NO176749C (no) | 1995-05-24 |
| JPS6470084A (en) | 1989-03-15 |
| KR890004780A (ko) | 1989-05-09 |
| FI97276C (fi) | 1996-11-25 |
| EP0306398B1 (de) | 1993-02-03 |
| IE882670L (en) | 1989-03-03 |
| NO176749B (no) | 1995-02-13 |
| DE3878098T2 (de) | 1993-06-09 |
| ATE85229T1 (de) | 1993-02-15 |
| PT88421B (pt) | 1992-10-30 |
| JPH0667409B2 (ja) | 1994-08-31 |
| FI884055A (fi) | 1989-03-04 |
| NO883893L (no) | 1989-03-06 |
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